


Uncertainty

by StarrySummers04



Category: Supernatural
Genre: Angels are cockblocks, Bisexual Dean Winchester, Castiel Has a Crush on Dean Winchester, Coming In Pants, Dean Winchester Has a Crush on Castiel, Dean Winchester Needs a Hug, Dry Humping, Episode: s04e07 It's the Great Pumpkin Sam Winchester, Episode: s04e09 I Know What You Did Last Summer, Episode: s04e10 Heaven and Hell, Episode: s04e13 After School Special, Episode: s04e14 Sex and Violence, Episode: s04e15 Death Takes a Holiday, First Kiss, Gay Castiel (Supernatural), Grinding, Kissing, M/M, Making Out in the Impala (Supernatural), Neck Kissing, Other Additional Tags to Be Added, Rating May Change
Language: English
Status: In-Progress
Published: 2020-11-22
Updated: 2020-11-24
Packaged: 2021-03-10 06:02:05
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,134
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27668590
Author URL: https://archiveofourown.org/users/StarrySummers04/pseuds/StarrySummers04
Summary: When sat on the bench with Castiel, some more truths are revealed about why the angels raised Dean and why they are following Dean's orders. Maybe Castiel is in a bit too deep already.Basically, I'm rewriting aspects of the show to include Destiel from the beginning.
Relationships: Castiel/Dean Winchester
Comments: 13
Kudos: 18





	1. 4x07: It's the Great Pumpkin, Sam Winchester

"I'm sorry, run that by me again. Your orders were to do whatever Sam and I told you to do?" Dean checked.

"Not you and Sam. Just you. You were the one I was instructed to raise from Hell. If they wanted me to follow Sam's orders then they wouldn't have needed to raise you from perdition." Castiel corrected.

"So, why me?"

"Because you're special, Dean. God seems to have big plans for you." Castiel replied. Dean signed deeply and put his head in his hands. "It does have something to do with what happened whilst you were in Hell."

"You'll have to refresh my memory. I don't remember a thing about my time in Hell." Dean stated.

"I know for a fact that isn't true, Dean. I know you've been having nightmares. Which is understandable. It was Hell after all."

"I don't suppose we could have this conversation some place else? I don't feel comfortable talking about this out in the open, especially not when there are children nearby." Dean explained. Castiel snapped his fingers and suddenly they were in

a motel room, but not the one he was currently sharing with Sam. Which was good. Dean didn't want Sam to come back and hear about his time in Hell. There was a reason he'd told his little brother that he couldn't remember anything.

"What I did is unforgivable. My time in Hell felt like it lasted centuries even though it was only 4 months."

"You know time works differently in Hell. It was 4 months up here but it was 40 years down there.'' Castiel reminded him.

"I hate it, Cass, and I hate myself."

"What happened wasn't your fault." Castiel tried.

"Well I disagree! Everything that I did in Hell was my fault. It was my fault that I'm not strong enough." Dean crumpled in a heap on the bed.

"It's not because you're weak at all, Dean. Everything you've been through since you lost your mother. Being raised as a hunter, always having to look after Sam. The way your father favoured your brother, the way nothing you did ever seemed to be good enough. Sam leaving to go to school, the arguments, your father going missing, then dying. Dean, you've been strong for so long. What happened in Hell was not a sign of you being weak. It was a sign of someone who has been strong for too long." Castiel rambled. Dean couldn't help but smile at the angel. No one had ever talked about him the way Castiel did. It made Dean feel weird inside, he didn't know how to respond to what the angel had said. Even Castiel seemed surprised, he wouldn't meet Dean's eyes armed there was a faint blush across his cheeks.

"Do you really think so highly of me?"

"Of course I do, Dean. You're a good man who bad things have happened to." Cass sighed.

"I tortured people."

"I know. They were in Hell for a reason though.'' Cass pointed out.

"So was I until you pulled me out. Why? Dean asked

"You are not a bad person. You didn't belong in Hell."

"I made a deal with a demon. Anyone who makes a deal gets sent to Hell. It's as simple as that. I knew that prior to making the deal. So why bring me back?" Dean requested.

"I'm not supposed to tell you." Castiel admitted, suddenly acting shy. Dean stood up from the bed and moved in front of Cass, backing up until Cass had his back to the wall and couldn't escape because Dean was standing so close. Castiel wouldn't stop his eyes from flicking to the hunter's lips. This action didn't go unnoticed by Dean. "Why not?"

"Those were some of my orders.''

"Besides, I don't want you to feel worse than you already do."

"And why would I feel worse?" Dean queried.

"Because you blame yourself for everything, Dean." Castiel breathed. He could easily get away but he liked being this close to Dean. Despite all the snark and sass, he really quite liked Dean, there was just something about the way the hunter

refused to take rubbish from anyone. Regardless of who they are. Dean brought up a hand to caress Castiel's cheek and the angel eagerly leaned into his touch.

"Please tell me." Dean whispered.

"Okay, but you'll want to sit down." Cass caved. He just couldn't help but want to do whatever Dean said. Dean pulled back from Cass and moved to sit on the endings of the bed, pulling Castiel to sit with him.

"Please."

"You have to be the one to stop Lilith from breaking the 66 Seals because you broke the first one." Castiel admitted. Dean immediately snatched his hand away from the angel.

"I broke the first Seal? How did I break the first Seal?" Dean question. The hunter wished he had any kind of alcohol right now.

"Dean, it's not your fault." Cass tried.

"How can you say that? I broke the first Seal and somehow that's not my fault?"

"You still don't know what the first Seal is, how were you supposed to safeguard against preventing it from being broken? Besides it could have been anyone that broke the Seal. It just so happens that it ended up being you." Castiel argued.

"So what's the first Seal?" Dean asked. Cass took a deep breath and Dean reached over to take the angel's hand again.

"You can't tell anyone that I told you. You're not supposed to know. They expected you to do whatever you're told but I've been watching you and your brother for the last couple of years and I know that's never been your style." Cass smiled, wryly. "It is written that the first seal shall break when a righteous man sheds blood in Hell. As he breaks, so shall it break."

"Well, that's comforting." Dean chuckled sarcastically.

"You didn't know." Castiel repeated.

"No. You're right. I didn't know. But it's still my fault."

"Don't say that. Not everything in the world is your fault. You've saved so many people. Done so much good. I don't blame you at all." Castiel said, honestly and Dean didn't doubt him. Dean couldn't help it, he leaned forwards and pulled Castiel in for a kiss, joining their lips. Castiel gasped in surprise and Dean took this as an opportunity to slip his tongue into the angel's mouth. Castiel had no idea what he was doing but Dean was always more than happy to show someone the ropes. Dean pulled away when the need for air became too much. Castiel couldn't stop panting, allowing Dean to lay down and pull the angel on top of him. Castiel was eager to learn and happily straddled the hunter without much encouragement. Dean laughed, he was sure that he would be destined for Hell now that he was well on his way to defiling an angel. Cass leaned down to kiss Dean again and the hunter found himself pushing the angel's trench coat off his shoulders. In the next moment, Castiel found himself under Dean. Castiel threw his head back and moaned when Dean attached his lips to the angel's neck. "Oh, Dean." Cass sighed.

"I've got you." Dean assured. Just as Dean was about to undress Castiel even more, Cass suddenly pushed Dean away from him and sat up.

"I have to go. I'm so sorry, Dean." He apologised.

"Hey, you're an angel. I'd be more surprised if you weren't busy." Dean smiled. He'd really been through the wringer with his emotions since he'd sat down with Castiel. But maybe things weren't as bad as they seemed. maybe Castiel had a point about things not being his fault. Dean couldn't help but hope that it wouldn't be long before he next got to see Cass. Besides, he really wanted to defile the angel.

"I'll see you soon, Dean." Cass offered, pressing one last chaste kiss to the hunter's lips as he hastily pulled on his trench coat, now in a rush to meet up with Uriel and head back to Heaven.

"Oh, I'm counting on it." Dean smirked, but Castiel was already gone.


	2. Chapter 2

"Sam?" Dean interrupted.

"Yeah?"

"Too much information." Dean told his little brother. He really, really didn't need to hear about how Sam was sleeping with a demon. "Sorry, I told you I was coming clean." Sam pointed out.

"Yeah, but now I feel dirty." Dean replied. He wouldn't help but wonder if sleeping with an angel would be anything like having sex with a demon. Or a human. It was quite obvious that he was going to have to take the lead when he and Castiel got there because the angel didn't even know how to kiss. So he certainly wasn't going to know what sex is or how to do it. "Well, brain-stabbing imagery aside, all you've told me about so far is a manipulative bitch who, uh, screwed you, played mind games with you and did everything in the book to get you to go bad.” Dean pointed out.

"Yeah, well there's more to the story." 

"Just, skip the nudity, please." Dean requested. God knows he usually leaves that out of the stories he tells Sam. His little brother doesn't need to know about that part of his life, so he doesn't need to know about that part of Sam. Honestly, after his attention had been moved onto Cass, he wouldn't stop thinking about the angel. Dean hadn't seen Cass since they'd kissed after the raising of Samhain and Dean found himself looking forward to the next time he was going to see the angel.

* * *

Unfortunately, the next time Dean saw Castiel, the angel insisted that they needed to kill an innocent girl. That certainly made Dean feel very confused. Then Anna banished the angels and they all packed up and headed to Bobby's. Thankfully, the older hunter wasn't in.

After finding out who Anna really was and listening to her explain her side of the story, things did make more sense to Dean. After a while, Dean just needed some fresh air - he'd taken Pamela home, Ruby and Sam were pouring over information that could possibly help them locate Anna's grace, and the fallen angel had gone to bed, which was understandable considering everything Anna had been through in the last 48 hours. Since he was alone, Dean figured it was safe enough.

“Cass? Are you there? Are you okay?” Dean checked, not really expecting a reply but desperately hoping for one at the same time.

“Hello, Dean. I'm absolutely fine." Castiel replied, appearing with a rustle of his wings.

"Where did you go? What did she do to you?”

"That was an angel banishing sigil. That's how you make something angel proof." Cass admitted.

“Does it hurt you?" Dean asked, finally getting his feet to move as he rushed over to Castiel's side.

"No. I'm in no pain." Cass smiled. "Good." Dean reached out and pulled Castiel in for a kiss that the angel was more than happy to reciprocate. "Wait," said Dean. "Before we take this any further, how could you be willing to kill Anna?”

“Honestly, Dean? I don't want to but those are our orders and I couldn't disobey them in front of Uriel or he would report back to our superiors and I could be forced to stop seeing you. Or I could and up like Anna. I completely agree with everything you said back at the cabin." Castiel explained. Dean smiled, he was so relieved to hear that. It had been bothering him since the altercation in the cabin.

“Okay, I feel better about things now that I know your true thoughts.'' Dean stated, pulling Cass in for another kiss.

"Are we going to take things further this time?” Castiel asked when the need for air became too much. They were both breathing heavily.

"Get in the car." Dean instructed, fumbling with the lock. He finally opened the door and ushered Cass into the backseat. The angel sat furthest away from the door and Dean got in behind him and slammed the door. Their lips joined with more heat now, Dean ran his tongue over Castiel's bottom lip to ask for permission to enter the angel's mouth. Unlike the first time they had done this, Cass had a bit more of an idea as to what was going on so he eagerly opened his mouth, encouraging Dean to tangle their tongues together. "Dean!" Sam shouted, sounding to be quite a distance away. 

"Shit!” Dean exclaimed, pulling away from the angel.

“I must go. Sam can't find out about this. Neither can the other angels. I'd be in so much trouble." Castiel explained, disappearing without another word.

"Dean?!' Sam tried again. Dean got out of the Impala so that Sam could see him. 

"There you are! What were you doing in the Impala?"

"Getting some shuteye. That's besides the point anyway. Have you got any leads?" Dean checked.

"Yeah. Ruby's gone to wake Anna.”

"Let's go then."

* * *

"Where have you been?" Uriel asked when Castiel reappeared.

"Dean Winchester asked to see me so I went to see what he wanted." Castiel replied.

“And? What did he want?”

"Nothing of importance. Hence why I'm back already." Cass replied. 

"I don't understand why you've decided to be at the beck and call of a mud monkey." Uriel stated.

"I've asked you once already to stop calling the humans that name." Castiel pointed out. “Besides I was ordered to save Dean Winchester for a reason. I figure the least I can do is go when he calls." Castiel replied. Uriel raised his eyebrows.

"Well, whilst you were busy doing whatever it was, I found where Anna hid her grace when she fell. It was inside an oak tree." Uriel stated, holding up a glass vial containing Anna's grace. Castiel smiled, trying to seem happy about this turn of events, he couldn’t have anyone question his loyalties after all.

* * *

Sam and Ruby explained how they thought Anna's grace must be in a tree in Kentucky so the four of them got in the Impala and set off for Kentucky.

Unfortunately, when they got there, Anna's grace had already gone. Dean was busy arguing with Ruby, much to Sam's annoyance when they all noticed that Anna was being very quiet. "Um, guys? The angels are talking again." She interrupted.

"What are they saying?" Sam asked.

“It’s weird... like a recording... a loop. It says 'Dean Winchester gives us Anna by midnight, or.'" Anna cut herself off. 

“Or what?' Dean asked.

“‘or we hurl him back to damnation.” Anna finished. Sam started asking about weapons that could trill angels, everyone was trying to come up with theories and Dean had had enough.

“Looks like I'm going back to Hell then, because we are not giving you over to Heaven." Dean told Anna.

“Dean..." Sam tried.

"Just... leave me alone, Sammy. I need some space. All of you, leave me alone." Dean warned before storming off outside.

"Really, Cass? After all the trouble you went to to get me out of Hell and they're just gonna throw me back?" Dean asked and heard the now familiar rustle of wings.

“It's an empty threat. Either you hand over Anna or the garrison will come and take her by force. I have nothing to do with this, it's out of my control. Uniel is beginning to question the frequent trips I'm making to see you." Castiel explained.

"Well, since you're already there, shall we pick up from where we left off?” Dean smirked. Castiel couldn't help but smile and nod.

Dean led Castiel to the backseat of the Impala again and they both removed their jackets before getting in and threw them on the front seat. Cass lay down and Dean got in between his legs and on top of him, joining their lips immediately. Dean used one hand to hold himself up as the other undid Castiel's tie and the buttons on his shirt. Cass moaned when Dean's lips found his neck and began to nip and bite at it. Dean pulled away and sat up long enough to remove his own shirt before getting back down to Castiel and sealed their lips in a heated kiss. Dean encouraged the angel to wrap his legs around his waist as they grinded against each other. They both knew that this was all they had time for and Dean couldn't find it in himself to be disappointed. He'd kissed multiple people since being brought back from Hell, but the only way he'd been able to get off so far was by himself with his hand. It was no longer cutting it. Dean kept a quick pace as the angel cried out at the friction between them. Castiel had very little idea what was going on but he was more than happy to go along for the ride and see what happened. "Dean... it feels so good!” He moaned and Dean smirked as he pulled Castiel in for another kiss. Cass let his left hand wrap around Dean's neck whereas his right found its way to the hand print he'd left on the hunter's shoulder.

"Oh, fuck, that's hot." Dean panted, picking up the pace as he chased his own release. Castiel felt as though his stomach was getting tighter and tighter until something snapped and he cried out against Dean's mouth. The hunter wasn't far behind and came in his pants, too. They panted into each other's mouths as they tried to catch their breaths. Dean pressed a chaste kiss to Castiel's lips before sitting up and beginning to pull his shirt back on. Cass stayed where he was laid but did up his buttons amid tie as they weren't completely removed.

"I should probably get going. Uriel will be wondering where I am and you should get some sleep." Cass advised when they were both presentable.

"I'll see you at midnight." Dean replied, pulling Cass in for one last kiss before the angel disappeared. Dean lay down on the backseat and closed his eyes. He was asleep within minutes.

* * *

Uriel visited Dean in his sleep, without Cass because apparently Dean was his weakness, because Castiel liked him. And then Dean had to lie, had to make Uriel think he'd had sex with Anna, just because he was defending her. Uriel couldn't know the truth, couldn't know that he'd been with Castiel instead. And then he was given the choice. Anna or Sam.

* * *

Sam seemed angry when he found out the next morning but Anna was indifferent. "I forgive you." She told Dean, pressing a kiss to his cheek. Dean wasn't blind, he noticed the glare Castiel sent in Anna's direction. And then Ruby arrived with the demons, sending everything into chaos. Sam, Dean and Anna stood out of the way, not wanting to get in the middle of a fight between Heaven and Hell. But when Alastair had the upper hand against Cass, Dean couldn't stand idly by. He had to do something. Alastair wasn't impressed that Dean smacked him around the head. Before Alastair could retaliate, Anna snatched vial containing her grace from around Uriel's neck and smashed it, reabsorbing her angel mojo. The demons quickly left, except for Ruby and Anna disappeared so Castiel and Uriel left.

When Ruby had gone, too, Dean finally opened up to Sam about what had happened in Hell. He didn't feel as though he could hide it anymore after Alastair’s comment. "I wish I couldn't feel anything anymore." Dean confessed.

And from where he was watching over the Winchester's, Castiel shed a tear for the pain and sadness he could hear in Dean's voice.


	3. 4x13, 4x14, 4x15

It had been a couple of months since Dean had last seen Castiel and he missed the angel. And Dean really wanted to see Cass again. He also wanted to kiss and touch the angel again but he would settle for just seeing the angel. "Cass? Are you there? It's been a while." Dean prayed. He didn't get a reply.

Sam noticed that Dean was extra cranky. He figured it was probably because of both the case they were working, considering that Dean had hated life at this school, as well as the fact that he knew his brother hadn't had sex in a while. Sure, he and Dean didn't spend every moment of every day together but, annoyingly, Sam could always tell when his brother had gotten laid, and it had been months since he'd got back from Hell.

"Dean, are you sure you're alright?" Sam checked.

"Why wouldn't I be?" Dean snapped.

"Because you're snappy and short tempered all the time and I'm sick of it. Also, you're not acting like you. When was the time that you got laid? Or that you hit on someone?” Sam asked. 

"Since when have you given a crap about my sex life?" Dean asked. "I don't ask about your sex life so you don't need to know about mine.”

Sam kept trying but he couldn't get anything out of Dean. In the end he dropped the subject but he knew there was something that his brother wasn't telling him but Sam decided to drop it for now.

* * *

After that case was over, their next case involved strippers and Sam figured surely Dean would start to feel better, act more like himself, especially when he'd sounded so excited. And then Dean made friends with the Siren. Dean told him nothing had happened with Nick, not that Sam cared, he knew Dean was bisexual. It wasn't an issue but it was the only lead Sam had about why Daean was behaving. "Seriously, what is going on with you?" Sam demanded.

“Nothing.” Dean snapped. 

"Is it that you want to have sex with another guy? Because you know I don't have a problem with your sexuality! Hell, if it will stop the way you're behaving then I would encourage it!" Sam exclaimed. It's a good job they didn't get everything off their backs when tattling in front of the siren. Dean didn't see the point in telling Sam that Nick had tried to seduce him first but that hadn't worked. He wears far too hung up on Cass to think about anyone else and that frightened Dean more than anything. He'd always been detached from his feelings, he knew love didn't last, or if it did, it could be used against you by any supernatural creature in the book. So Dean didn't get attached. And then

Castiel walked into his life. 

* * *

"Cass, please." Dean whispered, stood alone in an empty parking lot. But Dean was still standing there alone.

* * *

Bobby found them a case so the brothers headed to a town where no one was dying. And had a run in with Alastair. And decided that they needed to become ghosts to find out what was going on.

“Are you sure the angels aren't going to help us?" Sam checked.

"I've prayed to Castiel. on multiple occasions, Sam. Either they're not listening or they don't care. We're on our own." Dean snapped. Sam couldn't help but wonder if that was why Dean was so grumpy. He must be upset that he'd called Castiel and the angel hadn't shown. It was also really annoying that the angels wanted them to save the Seals but wouldn't offer them any help. It really made Sam question his faith.

* * *

Dean found it weird, having a heart to heart with a reaper but she wasn't going to be able to tell anyone.

"I take it you haven't told your brother that you've been trying to seduce the angel on your shoulder?" Tessa laughed.

"Jokes on you, it's been working." Dean replied. Dean probably would have said more if Sam hadn't come downstairs with Cole. And then they were busy. Again.

* * *

Dean was beginning to get fed up of all the run-ins with Alastair, but it was worse now. He was practically powerless as a ghost. And then Alastair was gone in a flash of lightning. "What the hell?" Dean asked himself.

"Guess again." Castiel replied. And Dean was furious.

"Seriously? You've been ignoring me for weeks, months, and now you show up?" Dean demanded. 

"You just saved the seal. This was a victory." Cass assured. 

"Why does it never feel like that?" Dean asked, but Castiel had already gone. Dean was disappointed, but not surprised.

Dean helped Tessa before being returned to his body, only to find Pamela bleeding to death. Their lives just seemed to go from bad to worse and Dean was sick of it. All the people that had helped them, had done so much good and they were never able to save them.


End file.
